Water → 5-(5-nitropyridin-2-yloxy)-1H-indole-2-carboxylic acid methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([OH:14])=[CH:9][CH:8]=2)=[O:4].Cl[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1)=[CH:9][CH:8]=2)=[O:4]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
5-Hydroxy-1H-indole-2-carboxylic acid methyl ester (0.845 g, 4.42 mmol) and 2-chloro-5-nitropyridine (0.771 g, 4.86 mmol) were dissolved in DMF (5 mL). To the solution was added anhydrous potassium carbonate (0.611 g, 4.42 mmol) and the resulting solution was stirred for 18 hours at 80° C. Water (80 mL) was added to the reaction solution and the mixture was extracted with ethyl acetate (80 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate and the solvent was removed by evaporation. The residue was purified by silica gel column chromatography (AcOEt:n-hexane=1:3), then the obtained solid was recrystallized from ethyl acetate and n-hexane to yield 0.753 g of the title compound as a yellow powder.
Aufarbeitung
- extractionthe mixture was extracted with ethyl acetate (80 mL)
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was removed by evaporation
- customThe residue was purified by silica gel column chromatography (AcOEt:n-hexane=1:3)
- customthe obtained solid was recrystallized from ethyl acetate and n-hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-145cb71ca4ac4cfd9b301e3e6a3ca599
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08551999B2
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